


The 40 Year Old Virgin

by Alphas__Pet



Series: The Demon With The Scruffy Face [7]
Category: Devil May Cry
Genre: Blow Jobs, Come Swallowing, Comforting, Condoms, Cute Ending, F/M, First Time, First Time Blow Jobs, Fluff and Romance, Fluff and Smut, Hair-pulling, Innocent Dante, Kissing, Loss of Virginity, Love, Making Love, Neck Kissing, Oral Sex, Romance, Sex, Sexual Fantasy, True Love, Vaginal Fingering, Vaginal Sex, Virginity, come tasting, safe sex, sick reader
Language: English
Status: Completed
Published: 2019-07-14
Updated: 2019-07-14
Packaged: 2020-06-27 23:44:21
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,754
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19800241
Author URL: https://archiveofourown.org/users/Alphas__Pet/pseuds/Alphas__Pet
Summary: Truth was Dante had never done anything before. It was a bit embarrassing to be as old as he was and not have had sex yet. Though he did know a thing or two, he'd just never gotten around to trying things out before.





	The 40 Year Old Virgin

**Author's Note:**

> Got the idea while literally watching The 40 Year Old Virgin lol. I was like hey! We all know one of those ^_^ So I wrote a quick little something.
> 
> As always, I've tried to get all those errors but I've noticed even after re-reading things four times over I still have errors lol. Our brains read words that are misspelled and spell them correctly in our minds even though our eyes see differently so I apologize if you stumble across any lol.
> 
> I hope you all enjoy this! I thought it was pretty cute ^_^

"Dante! You coming with us tonight?" Lady took a bite out her slice of pizza and leaned against her best friend's desk.

"Not to night, my girl is sick and I'm going to go over there with her." Dante brought his legs down from his desk and grabbed a slice of pizza for himself.

"Oh yeah, I forget sometimes you have a girlfriend." She rolled her eyes and stood up right. 

"Well, what are you two going to do tonight then?" She smirked and nudged his shoulder. 

"Nothing, I just told you that she's sick." 

"What's that supposed to mean? You know what will make her feel better, don't you?" 

Dante just rolled his eyes and went to grab a beer. "I'm sure you know all about that." 

"So you mean to tell me you've never just given it to her after a long stressful day?" Lady followed right behind him, hot on his trail.

It was only right that his best friend dig in his personal life, since he would often do the same. He was just excited Trish wasn't present to torment him as well. Those girls worked Dante's nerves, but they were the best handy women he could ever ask for. If he needed help getting a job done, he'd definitely knew who to call. 

"Given her what?" Dante gave Lady a raised brow look and went back behind his desk.

He knew very well what, _'it_ ' was she was referring to, but he'd rather not discuss it. 

"You know!" Lady smacked her face with her palm and shook her head. "You know exactly what I'm talking about. You've been dating this girl for a while and I have yet to hear any stories!" 

"I don't kiss and tell." Dante shrugged and threw his legs back up.

He wished a job was ringing his phone at the moment because he absolutely didn't want to talk about his intimate life; even if it was with his best friend. 

"Aw, come on! I tell you stuff."

"You tell me too much stuff sometimes." Dante chuckled and shook his head. 

"Why do you want to know so bad?"

Lady shrugged and grabbed another slice of pizza; dusting her top off and taking a seat on the loveseat adjacent from the man's desk. 

"Just making conversation before you leave us for the night." 

By _us_ she meant her and Trish. 

The women wanted their dear friend to tag along on a job they had but Dante had other plans and they both knew better than try to convince him to abandon you for the night. Unless they absolutely couldn't handle it then his answer would always be no. 

It kind of sucked that they didn't get to spend as much time with the man as before but both girls were happy to see him finally in someone's face and out of the pages of his many kinky magazines. 

"Ah you always try and make me feel bad; well it won't work this time!" Dante sipped his beer and leaned back in his desk chair.

"Not tonight, but I'm telling you, you want to make her feel better you'll go in there naked and give it to her right there in the doorway." 

"What the hell is wrong with you?" He laughed and shook his head. 

It was a reason Dante was avoiding all the sex questions.

"Just trying to help you out! Surely you want to get laid, don't you?" 

Dante just shrugged. "Can we talk about something else?"

"Ugh, Dante you always get like this when we talk about sex. What gives?" Lady inquired. 

Her two toned eyes were locked on her best friend who was deliberately avoiding her gaze. 

"You two _have_ done it, right?" 

"...No." 

She gave the man a quizzical look since that wasn't the answer she was expecting. "Wait, so you're still a-"

"Yes! Don't you dare say it." 

Lady shook her head and jumped up from her spot to sit on the edge of Dante's desk. 

"You know I wouldn't make jokes about that, but haven't you been dating for like 5 months now?"

"Yeah... I don't know okay? We just never got around to it..."

"Does she know?" 

"No..." 

Truth was Dante had never done anything before. It was a bit embarrassing to be as old as he was and not have had sex yet. Though he did know a thing or two, he'd just never gotten around to trying things out before. 

His luck with women not one to brag about. 

"Wait... so has it not came up before?" Lady was no intrigued as to why her best friend and you hadn't gotten it on yet and you were almost at the halfway year mark of your relationship. 

Either you were really patient or getting laid somewhere else. Surely you'd want to sleep with Dante as much as he wanted to sleep with you; she thought. 

"Well yeah... but-"

"So what do you tell her??" 

"Oh God, why is this so important to you?" Dante groaned and threw a magazine over his face in hopes Lady would disappear. 

"I'm just trying to understand why you haven't had sex with your girlfriend and you've been dating for 5 months!" 

"I just tell her I don't feel good or I'm tired; shit I don't know. Stop making a big deal about it!"

"I'm not! I just think that you should at least tell her the truth, so she doesn't get the wrong idea..." 

"She never says anything about it.." Dante shrugged. 

"Well still, maybe tonight should be the special night..."

"For the last time insane woman, she's sick."

"Okay, she's sick; not dying. Go out and get her some soup then surprise her with your dick in it." Lady laughed and pushed Dante's chair, almost making him fall.

"That's a terrible idea, didn't Trish need your help?"

"Aw, come on! Just at least talk to her about it." 

"Fine, if it'll shut you up I'll tell her." Dante groaned, already dreading the conversation he was going to have with you. 

Eventually he would have to tell you since he always avoided it when the time came. You'd be in the middle of making out and your hands would go down to his belt, but he would always stop you and change the subject or just ultimately move away from you all together. 

You supposed it was a personal reason as to why he always denied you intimacy and part of it was, but Dante was just too embarrassed to tell you he was a virgin. You loved him though and would accept him either way, however. 

*****

"Thanks for coming to spend the night with me, babe." Despite having a cold you mustered up a warm smile and hugged Dante's arm. 

"Of course. I know you must be miserable being inside all day." 

"Oh definitely. I can't wait till I'm better though." 

You finished your soup he'd brought for you and your orange juice before turning your attention towards your boyfriend. 

"You're the best." 

Dante just gave you a smile and kissed your damp forehead since you were perspiring from the fever you had. You felt like shit, but it still wasn't enough to bring your mood down. 

"Anything for my baby." 

"Mm I'm so lucky." You pulled Dante into a kiss. 

Luckily he had demonic blood that kept him from catching your sickness because now you had your tongue in his mouth and dirty sneeze hands all up under his shirt. 

The making out was arousing both of you and when you felt his hardness nudge at your sex and tried to go for his belt like you always did but he stopped you. 

"No, you're sick, babe." 

"Yeah but you've been making out with me the last 5 minutes. I think I'm okay to do stuff, you want to?" You smirked and pushed your top up. 

Dante watched you as you just sat there in your bra and lounge shorts. He wanted to touch you, but he couldn't gather the courage to since he knew what it would lead to. 

"Not tonight..." 

You pouted and took his hands. "Baby, are you seeing someone else?" 

"What? No! Why would you ask that?" Dante squeezed your hands and gave you a knitted brow look. 

He knew you were probably assuming the worst and he hated that he was keeping things from you, but he didn't know exactly how to come out and say he was 40+ years old and never been inside anyone before. 

"...Because we've been dating for almost half a year and you've yet to make love to me... am I not attractive?"

"Babe, of course you are! I know you can feel that you're attractive to me." Dante moved his hips up into yours and you giggled a bit since his hardness was nudging you. 

"It's not that at all..." 

"Then? What's wrong? You can tell me. Is it not big or something? Because that doesn't matter to me." 

Dante laughed and shook his head. "No, that's not it either." 

"Okay, so what's wrong then? Why won't you touch me?" You moved closer to your boyfriend and tried again to unbuckle his belt, but Dante wouldn't let you. 

"Do you not like girls?" 

"Babe..." 

"What! I'm just trying to figure it out is all..." you sneezed and looked up at him.

You whole face was on fire and you felt like you head would explode but you had enough spare energy for some fun. If your boyfriend would ever get with the program.

"You don't last long or something?" 

Dante just shrugged. "I don't know." 

You looked at him a bit confused. "What do you mean you don't know? How long did you usually last with other girls?" 

Dante didn't answer you and you began to get frustrated with his lack of explanation. 

"Dante! Come on..." 

He sighed and took your hands. "It's none of those things and it's not you, I promise it's not you. It's... I've.." he took a deep breath. 

"I um... I've.. n-n-never d-d-done it be-before." He shut his eyes and his cheeks tinted the prettiest shade of pink. 

Dante was a bit surprised to feel you squeeze his hands tighter and touch his face. He slowly peeled one eye open at a time to see you sitting in front of him smiling. 

"Really? Is that what's been bothering you?"

He nodded and looked away from you. "Oh, God. I'm going to go sleep on the couch tonight-" 

He tried to retreat from you, but you didn't let him. 

"No, don't. I want you to stay up here with me." You smiled and moved so you were sitting cross legged. 

"This is highly embarrassing." Dante laughed awkwardly.

It did however feel good to finally tell you the truth of why he'd been avoiding you. He really liked you and wanted to experience his first time with you, but he just couldn't bring himself to actually begin when the opportunity was presented to him. 

"Don't be. I'm not laughing at you. I don't think it's funny or if you're thinking I think you're lame then I don't think that either." You assured. 

"I just thought maybe you practiced celibacy. Um, if you don't mind me asking, why haven't you?" 

Dante shrugged. "I dunno. I guess I never really got around to it. I tend to get busy sometimes and sex will be the last thing on my mind and whenever I'd try to find a girl; I usually just get the cold shoulder. Or attacked someway." 

He chuckled. "Never really had much of a girlfriend until you either... yes I know, what the hell is wrong with me." 

You shook your head and squeezed his hands. "That's impressive. You're quite the catch I can't believe no chick has given you the time of day, but I wish I could have waited to lose mine. I hate who I lost it to." You rolled your eyes and thought back to your first love. He obviously wasn't your true love, or you wouldn't have been mentally killing him with a fork.

It surprised you a bit to hear that Dante had never had sex, but it made you love him even more knowing that you could potentially be his first.

"Well, you're beautiful so I'm sure guys were after you left and right. At least you had someone willing to sleep with you." He laughed. 

"I would have slept with you if you asked." You smiled and reached to touch his face. 

It was your way of saying that you wanted to sleep with him but only when he would be ready. You didn't want to rush things and if Dante would never be ready then you wouldn't care. You enjoyed just spending time with him since he made you laugh and smile nearly all the time. 

You loved being around your boyfriend and just laying down and cuddling. Sure sex was fun but the bond you two shared was worth more than getting off. You didn't want to scare him away by forcing him to sleep with you and you were sure that despite being together for 5 months; there was a reason he still hadn't attempted to be intimate. 

So you just let things flow and hoped that Dante would continue to open up to you.

"..Really?" 

"Mhm! I wouldn't have mind one bit. You're so sweet and whatever girl gets lucky enough to be your first; I'm sure you'll be great to her." 

"Well, I was hoping that you would be my first..." Dante's cheeks lit up like a traffic light and he looked away from you since you had a big grin on your face. 

"I would love to be your first, Dante." You leaned forward slowly and kissed him. 

He kissed you back and held your face with one hand while his other put both of yours on his belt. 

You broke your embrace to look at him for clarification. The last thing you wanted to do was make him feel pressured into sleeping with you. Though you wanted to like crazy; you were fine with waiting until he was ready. However, now that Dante seemed ready; you weren't. 

"Wait.. you want to? Are you sure?" 

Dante just chuckled a bit. "I'm not getting any younger, so why not?"

You stroked his cheek and pushed him back. "Oh, Dante. I'll make it so special for you." You smiled and moved down so you could unbuckle his belt.

*****

"Are you nervous?" You stroked the inside of Dante's thigh while you two laid in somewhat darkness. 

The top ceiling light was off, but you still had a great deal of brightness coming from your lamp in the corner of your room. 

Despite being sick you wanted your boyfriend's first time to be something he wouldn't forget. You managed to get him down to his boxers; you being in your bra and panties and now you were about to kick things off. 

"No. I don't know.... maybe? I guess. I don't know but this is weird." Dante laughed a bit. 

"Aw, it's okay to be a little hesitant at first, baby. I won't rush you..." You sat up on your elbows and sneezed. 

"You sure we should be doing it and you're sick?"

"I'm fine! Just got some lasting sneezing." You got up from bed before disappearing in the restroom. 

Dante just chuckled and shook his head at you. His first time would be with his sick girlfriend who had to take breaks so she could go blow her nose or cough out one of her lungs. 

It was definitely going to be a first time to remember.

*****

"Okay, I'm back." You sounded a little less congested and your nose wasn't leaking like a faucet anymore. 

"So, um... you've never done anything at all with a woman?" 

"Does in my mind count?" Dante had his eyes closed but his cheeks were so pink, and his bottom lip was between his teeth. 

It was beyond cute and you couldn't help but to rub your hand up the imprint in his boxers. You knew it would probably scare the shit out of him but there was really no slower way to go about things. You'd made out for like 20 minutes already, so you decided to get him going by instructing him to tell you about some of his fantasies.

"What?" Dante sat up and looked at you.

"Tell me what you think about." You smiled and kissed his stomach. 

He had goose flesh all over and you wanted to squeal at how cute it was that he was so nervous but wouldn't admit it. A completely different man than the cocky, smart mouth stud you met in the beginning.

Dante seemed like a hard ass but deep down he was such a sweetheart; to you anyway. 

He opened doors for you and held your hand when you crossed the street. He always asked you how you were feeling and if it was anything he needed to work on relationship wise. 

Everything he did made you smile, and you felt honored to be able to share such a touching and personal moment with him. It made you love him more; you loved him before but now you were for sure it was true love.

"Stuff..." Dante was chewing at his lip again.

"Well what kind of stuff, silly!?"

"Um, naughty stuff." 

You gave him a pressed look and clasped your hand to where it was perfectly laying over his hardness, but you didn't move your hand or squeeze your fingers. 

You just left it there; feeling him twitch with excitement and push against your palm. 

"Tell me about these naughty stuffs, baby." You smiled and slowly drug your palm against his length. 

Dante's eyes slipped shut and it took him a second, but he began painting you a picture.

"I feel like a damn teenager but anyways, well I think about you a lot... and um-" He let out a heavy sigh. "Ugh! I can't do this. Sorry it's so weird to talk about this as old as I am."

"It's okay, baby. We can stop. We don't have to-"

"No, no. It's fine. I'm just being weird is all. I'm not used to a girl actually wanting me in bed." A faint laugh left his lips. 

Dante cleared his throat and started again. "Well I think about you and we're doing st- Ah forget it. Basically I'm screwing you on my desk or whatever, but we have to be quick since I have to leave, and you beg me to stay but I tell you no. So you just start kissing on me and then boom! We get started and from outside we can hear the girls calling for me but I'm telling them to give me a minute and not to come in." 

Your hand was still over Dante's hardness and with every word he spoke the more his length twitched and leaked. You could feel the warmth of his _pre_ soaking the fabric and you yourself was starting to get turned on as well.

"Yeah? What else happened, baby? Tell me more." You slowly moved your hand up and down; your fingers clasped over the thick flesh as he continued to tell you about his fantasy.

"So they're telling me to hurry up; surely they know what's going on. I mean they aren't stupid, but anyways I have my hand over your mouth to stop you from being so loud and you're just there taking me."

Dante moved his hips up into your hand's movements and you just smiled and kept going. 

"Mm that sounds like fun. What else happened?" You ran your hand down your bare stomach to your clothed sex. 

You made sure that your boyfriend had a full view of you touching yourself to his words. You wanted him to be the one who was in control for his first time. You would help him through if he needed it of course but you didn't want Dante to feel like a kid or uncomfortable. 

"So this whole time you're bent over the desk and I pick you up and lay you back and start screwing you that way. Your tits are just bouncing on your chest with my every movements. You look gorgeous and you took my hand and started sucking my fingers." 

Dante watched as you did exactly that. You removed your hand from yourself but kept the one you had on his length. 

He groaned when your swirled your tongue over his index and middle digits. You wrapped your lips around them and slowly began bobbing your head back and forward before pulling the fingers away with a lewd pop. 

"Y-yeah. It was just like that."

"What else were we doing, baby? Did I get on my knees for you?"

This was your way of saying you wanted to go down on him. He was more than turned on with how wet the front of his boxers were from his constantly leaking. 

You were extremely curious to see how he taste.

"N-not in this one but in another you did..." 

"Really? You should tell me about it then." You gave him a warm smile and kissed the skin right below his belly button; your lips getting tickled by the strip of curls there. 

"Okay, well we were out on a trip and everyone was sleep but me and you. We were in the van; me in the driver seat and you in the passenger. Anyway, all the girls were asleep and so we started talking and then we ended up kind of cuddled up just watching the stars." 

You continued to just pepper Dante's soft skin on his tummy with sweet kisses. You working your way up to something bigger and also stalling for time since you felt like you needed to sneeze again. 

"I love cuddling with you. Did we make out?" You asked.

"Yes, that's how you ended up with your face in my lap. At first you didn't want to because one of the girls could have woken up at any time, but I kept kissing your neck since I know it turns you on and you were like fuck it and just got to business."

Dante was so wrapped up in his tale that he didn't even noticed how you were edging down the waistband of his boxers.

"How'd I start, baby?" You cleared your throat; ready to make his fantasy a reality. 

"You were kissing all over me and like, licking different spots."

You wiggled his boxers down his hips and out bounced his amazing length. Your boyfriend was far from small and you couldn't believe you thought that, that could have been his reason for not wanting to have sex. Dante was gorgeous naked, and you definitely couldn't wait to feel him inside you.

*****

You just took a couple more second to admire the thick flesh; the way it leaked pre droplets onto his stomach, you couldn't resist the urge to lap them up, so you cleaned his tummy before doing exactly what he said you were doing in his fantasy.

"Like this?" You hummed and wiggled your tongue against the few veins coursing through it. You kissed every span of flesh you licked before ultimately stopping so you could hear the rest of his story. 

Dante opened his eyes to watch you. It was a bit weird to have someone else touch him below the belt but what you were doing felt great so he continued with his fantasy the best he could. 

"Y-yes. Just like that..."

Small pants fell from his lips and you had to control yourself in order to not rush things and just take him down. 

"Mm tell me what else happened, baby. It sounds like you have a lot of sexy day dreaming time." 

"I think about you often. Um, well next you started to actually suck..." 

"How? How was I pleasing you? Like this?" You stroked him a couple of times before very slowly wrapping your lips around just the head and sucking. 

Immediately you were greeted with a flavor that made your mouth water and taste buds ignite with sparks of lust that you just wanted to douse with his seed. You had to stop yourself from just going crazy and showing Dante just how long you'd been wanting to savor him.

"Fuck... y-yeah. Like that. But you had m-more in your mouth."

You nodded and gradually took more inches of his length down; only focusing there for a moment while he enjoyed getting his first blow job. You didn't expect Dante to last very long for the night, but you promised yourself to make it the best however many minutes he was able to go. 

"Ah, shit. That feels good, babe." Dante wasn't sure if you wanted your hair tugged on or not, so he just ran his fingers through it instead. 

His hips kept leaving the bed, but he would almost immediately stop. Blow jobs felt great and he wanted to feel more but not get too carried away with you. 

You pulled away to gather your breath and to tell him to continue his story. 

"What else did we do, love?" Your hand lazily stroked him. 

"Um, well you did it until I... ya know..." Dante blushed and laughed. "This is ridiculous." 

"Do you want to stop? Are you uncomfortable?" You remained as serious as you could despite your boyfriend's awkward, embarrassed laughter. 

You didn't want to joke with him about the situation because it wasn't a humorous manner. If you both were being silly about the situation, then it would never happen, but you wanted it to happen. You wanted to be Dante's first. 

"No, no. You have to excuse me; this is all new to me so sorry for being so awkward." 

"It's okay, I know it can be nerve racking, but we can go as slow as you want. If you want to do that then you can." You smiled and took his hand. 

"I'm curious as to how you taste anyways." 

Dante nodded and laid back. "Okay..." 

He let you go back to blowing him and he just relaxed and enjoyed it.

*****

"Wow, babe." Surprisingly Dante hadn't erupted down your throat yet. 

You kept things slow; only suckling on four inches or so, leaving your hand to stroke the rest. Your tongue swirled all over the tip of his length; his manly flavor making your taste buds water with the urge to up your actions. 

So you did. 

“Is it like your fantasy?” 

Dante nodded so you went back down on him; your tongue flickering across the slit and gathering up the pre that continued to ooze there.

“Y-yes. Keep g-going.” His grip tightened in your hair and before he knew it, he was working his hips up into your mouth. 

You just smiled and pulled off. “Okay, I’m about to really get into it, are you ready baby?” 

Dante blushed a bit but nodded. “Yeah... I’m ready.” 

*****

Your hand gripped around his length at the base; a lose grip so his hard flesh could just glide through your limb as he lazily rocked his hips up. Dante looked too cute just getting himself off with the help of your hold. 

"I'm excited to screw you." He laughed and opened his eyes to look at you. 

"I'm excited too, baby. I can't wait. I know you'll do good."

"I apologize if I don't last very long."

You smiled and shook your head, "It's okay. As long as you enjoy yourself." 

You tightened your grip now causing some resistance in his thrust. The pressure of your hold felt good and with you suckling just the head; the saliva that dripped down into your grasped added to the pleasure. 

"Fuck." Dante pushed your head down more gently. He was getting used to getting blown and now he wanted to see what exactly all it was you could do. 

"Suck more, babe. Please?" 

Your boyfriend was so polite and gentle the whole time you were being intimate. A nice gesture since most guys wouldn't ask please for anything. 

"Of course." You smiled and got to bobbing your head up and down.

You worked your mouth horizontally on his length; the leaking head occasionally knocking the back of your throat but this wasn't your first rodeo, so you knew how to ride. You relaxed and let Dante take over. He was so wrapped up in his fantasy world on top of the pleasure you were providing him that he didn't even noticed he began to fuck your mouth and spew dirty words.

"Fuck yes, babe. Letting me shove myself down in your mouth is so hot." Dante's fists were tangled in your hair; his hips spiking up and his strong thighs meeting the skin of your cheeks.

You'd given blow jobs before; however, you'd never taken someone's whole length down like you were currently doing your boyfriend's. It had to be the realization that you were about to take his virginity that had you sucking like a squid. 

"Yes, ah! Right there!" Dante dug his heel in the bed, and he could feel his stomach tighten; his orgasm was close, and he couldn't decide if he wanted to empty it down your throat or push you off. 

The wet sound of your saliva gathering in your mouth and the many _acks_ you were making was enough for him to decide. 

"Baby, stop!" Dante huffed and tried to push you away, but he already had shot two spurts of his orgasm in your mouth. 

"Shit." He groaned and gripped himself around the flushed head of his length to try and contain his shower. 

"It's okay!" You removed your boyfriend's hand and stroked his spurting hardness right onto your face and breast. 

You moaned as your cheeks and lips were doused in his fresh seed. So warm and genuine since it was produced from more than just his hand.

*****

"Whoa..." Dante calmed from his first orgasm made by a girl. 

"How was it?" You inquired, his seed dripping down your cheeks. 

You used your thumb to taste some and surprisingly the was quite delicious. So you instructed him to help you clean the mess he made. 

"Baby, that was really good. I liked that a lot." Dante flushed red and drug his index finger around your face before pushing his orgasm into your mouth.

"Mmm, I did too. You can do it in my throat next time if you want." You winked and licked your lips once your face was clean.

You stepped to the restroom for a brief moment to clean your face and rid yourself of your snotty nose. It wasn't anything sexy about being sick while giving a blow job; you feeling like you couldn't breathe half the time, but you didn't want to delay your boyfriend's special moment any longer. 

*****

When you reentered the bedroom you were surprised to see your boyfriend sitting on the edge of the bed. 

"What's wrong, baby?" You kneeled down in front of him and picked his gorgeous face up to look at you. 

"I'm kind of nervous. I mean... I shouldn't be but I just feel like this would have been a lot easier if I was 18 again." Dante laughed awkwardly. 

He was nervous again and you found every bit of it cute.

"What's wrong with my cutie pie being a little older and losing it?' You smiled.

"You're so good to me. I'm glad I'm going to experience this with you." Dante held your face and pulled you back on the bed. 

"Even if you're a sneezing disaster right now." 

You gave your boyfriend a pressed look but kissed him soon after.

*****

You two engaged in a very touchy make out session and Dante asked to try going down on you, but you objected since you couldn't wait to feel him inside you.

He could show you what he knew next time. 

"Wait." You reached over in your side table and fished out a box of condoms. 

Dante just gave you an uncertain look and he automatically assumed the worse. 

"No, baby. It's not what you're thinking. I got these when we first started talking just in case we did have sex. Look, it's not even open." You showed him that the box was indeed sealed shut.

"I hope they're still good." You laughed nervously and checked the expiration date.

Luckily you didn't have to go to the store to get any. You opened the box and took one out and handed it to him. 

"Um, do you know how to put one on?" 

Dante didn't answer nor look at you; his adorable flustered face answering for him. 

"Aw, it's okay, baby. Come here, I'll show you." You gave him a comforting smile and carefully removed the delicate piece of latex from its wrapper.

"Okay you want to make sure you leave some room so when you... ya know, you don't end up breaking it or it goes back inside me." 

You carefully rolled the condom down his length; making sure to leave a space at the tip. 

"And that's it! Though, I think you may need something with a little more room." You blushed since your boyfriend had a bit to work with.

"Is it too tight?" You doubled check to ensure Dante wasn't being squeezed to death as if he had a rubber band tied around his finger.

"No, it's fine." He cleared his throat and touched himself. 

It felt a bit weird to have something on his length but safety first!

*****

"Whenever you're ready, love." You got next to him and laid down; tugging his arm so he could get on top of you. 

Dante took a deep breath; this was about to happen. 

Finally he would get to experience what sex really felt like and not what he thought it did. Blow jobs felt great, but he imagined you felt like the finest silk.

"Okay, I'm ready." He moved on top of you and you helped him adjust your legs so that you both were comfortable. 

You kept him hard by making out with him again and working your hips up into his. 

"I know you'll fuck me good, baby. You're amazing and I love you." You gave your boyfriend a sweet kiss before holding his lower back. 

You didn't want to rush him, but you didn't want him to feel like he had to do all the work either. 

Dante kissed you back and moved down to your neck. "I love you too. Okay... um, I think I want to start now..." he blushed and shut his eyes. 

"Okay, want me to put it in or?" 

"No, I will just... give me a second." He sighed and tried to keep his mind swimming in a pool of dirty thoughts since he kept going flaccid. 

"Okay, baby. However long you need, take your time, my love." You nodded your head and relaxed beneath him. 

Dante just spent the next 5 minutes kissing your breast and your neck until finally you felt him move his hand between your flushed bodies. He hesitated at first, but he gently touched your sex; the soft prickles of hair tickling his fingertips. 

"It's nice..." He admitted and he pulled his hand away quickly. 

"You can touch it. I like it." You guided his hand back down to your pearl and showed him how to rub you.

A soft moan fell from your lips as you humped Dante's hand.

"Put your finger inside." You gasped and showed him exactly how to please you. 

Dante caught on quickly and even surprised you at how skilled he was. He may have never had sex but that didn't mean he didn't know about things. His thoughts always helped him out and he couldn't wait to show you what he knew. 

"Fuck, okay. I'm ready." He pulled his wet digits from your body and guided himself towards your entrance. 

"Ready, baby girl?"

You nodded your head and grinned, "ready, baby boy." 

*****

Both of you gasped in sync as Dante pushed inside you. 

First of all, he was nowhere near small and you had to stop him from destroying your insides. 

"Wait, baby. Go slow." 

Dante laughed a bit, "Who's the virgin here; me or you?" 

"Well shit I didn't think you'd be so..."

"And it's a shame I got all that and no one to penetrate." 

"Mm you do now, baby." You hooked your legs around the back of his and gave him the okay to move. 

Dante sat there for a moment to calm himself before he showed you what he always dreamt about doing to you in bed. 

"I sure do, and you'll be nice and teach me new things, won't you?"

"Of course, but it already feels like you know a thing or two?" You gasped when he moved his hips. 

"I'm a virgin not living under a rock, babe." He chuckled and leaned down to kiss you. 

"I know some stuff; here, let me show you." 

Dante had his hands on either side of your head while he slowly rocked his hips into you. His eyes were shut, and his head slightly thrown back; and the way he keep biting his lip and swearing was turning you on something fierce. 

"Fuck, you feel so good." He panted. 

"So do you. Keep going." You moaned and grabbed his lower back and pulled his hips into yours even more causing a deeper penetration. 

You were surprised at how good your _virgin_ boyfriend could stroke. It was almost too good to believe he'd never done anything before with how he kept nudging your spot. 

"Oh, Dante! Yes fuck yes!!"

Dante tried to focus his mind on something other than how tight and wet you were. He couldn't feel your warm walls directly, but he could definitely _hear_ them vocalizing their want for him to fuck you harder. He wanted to last twice as long as he did for his blow job, but you just felt so good and the way you were howling let him know that either you were a damn good faker or he truly was screwing you really well.

"I wish I could feel you for real." 

"Mm, I might look into birth control if you're going to be fucking me like this every time." Your arms got pinned above your head by his hands while he slowed his movements down to deeper and more planned strokes. 

You nearly passed out at the new pleasure and you dug your heels into his sides when he used one of his hands to bring your leg up on his hip. 

"See, I've been learning for a while. Just never got to practice." Dante laughed and gave you a sweet kiss. "What's wrong? You looked surprised." 

"I am, fuck." You moaned when he pulled out and pushed back in. 

"Y-you sure you're a v-virgin?"

Dante chuckled and nodded his head, "haven't been in a woman since I came out one."

You just laughed a bit and brought him down to kiss him. "I believe you." 

"Can we try a different position?" Dante asked as he stopped his movements all together. 

"Of course, baby. What did you want to try?" 

"Um, lay on your stomach and put your butt up." 

"Are you going to pull my hair and grab my ass if I do?" You smirked and carefully turned over. 

"If you want me too, but I don't think I will last long like that. That's how I think about doing you in my fantasies and I never make it more than five minutes."

Your boyfriend just blushed and shook his head. You loved how open he was about his kinky thoughts. It warmed your heart even more to know you were a part of them.

"Aw, it's okay. Let's try it anyways." You smiled and arched your back for him. 

Dante got behind you and pulled your hips back. "Okay, don't be upset if this is a quick five minutes." 

He found your entrance before sliding back inside you. Again, both of you gasped at the feeling of each other. 

"Fuck, Dante. Mm that already feels good." 

"Yes it does." He groaned and gripped your hips tight. "I don't think I'm going to make it." Dante laughed and moved a bit. 

"Wow, babe. You feel so good like this. I'll try my best to give you more than three strokes." 

Slowing things down probably wasn't the best idea and going faster didn't seem like an option either, but Dante didn't want to disappoint you, so he went fast anyway. More of a steady medium pace but you wanted him to speed up. 

"Fuck yes! Faster, Dante." You let your shoulders touch the bed so you could reach under your body and spread yourself more.

"How does that feel?" He hesitated at first, but he smacked your ass; not hard which made it fucking adorable and because he was blushing so damn much. 

"Mm, harder, baby. I can take it."

"I don't want to hurt you..." he said as he rubbed the spot he'd just assaulted. 

"You won't. It's okay, you can be rough with me."

You caught your boyfriend by surprise when you began rocking your hips back; fucking him instead. Dante just groaned and held your hips even harder; giving spanking you rough a try. 

The stinging sensation left behind from his hand made you up your efforts into throwing your ass back even more. 

"Fuck yes! Dante, fuck. Pull my hair, baby." 

The tug he gave--a child could have drug you across the floor. 

Dante didn't want to hurt you even though you gave him permission too. He'd never had a girl tell him to pull her hair or to smack her ass while he fucked her roughly from behind. All this was new to him; physical wise. He knew about all the hair pulling and ass smacking; he'd just never done it.

"Harder." You whined and wiggled your hips so your ass could shake. 

This really got him going because now he had a fist full of your hair; your head yanked back and a handful of your ass while he fucked you so hard your body went flat against the mattress.

"Yes! Yes baby. Oh, you're doing so good!" You had a mouthful of your bed sheet as Dante put most of his body weight on yours. 

Your body was straight under his and with your legs being forced to be together made things... _tighter_.

"Shit, babe I'm not going to last much longer." Dante groaned in your ear. 

His left hand was still tangled in your hair while his right was intertwined with yours. 

"Mm it's okay, my love. Let it out, tonight was for you." You kissed his knuckles and turned your head to the side so he could kiss you. 

"Ah, I love you, _*name*_." Dante gave you a sweet kiss and pushed your face back in the blanket. 

He was becoming comfortable with being rough with you and if he was too much then you would tell him your limits. 

"I love you too, baby. Mm, yes!!" You gasped as your orgasm washed over you leaving you twitching underneath him. Your body constricted around his length and made him stop his movements. 

"Fuck, did you just?" 

You moved the blanket away from your face and smiled. "I did. That was amazing. Now you get yours, baby. You deserve it." You were still holding Dante's hand, so you kissed his knuckles again.

"Really? Was I good?"

Dante rocked his hips into you about six more times before he was groaning in your ear and squeezing your hand really tight.

"Shit..." He shook a bit and fell on top of you. 

"Mm, yes baby. You were so good." You smiled once his breathing calmed and he wasn't as twitchy.

*****

"Are you okay?" You picked your head up and glanced over your shoulder at your now not a virgin boyfriend. 

"Hm? Oh, yeah. That was just really fucking good." He laughed. "At the end; you got really tight and it was just too much. I couldn't keep going."

"It's okay, baby. You did really well for your first time."

Dante carefully pulled out of you and got off the bed. You showed him how to take off the condom without anything spilling out and how to just toss it in the trash. 

He ended up burying it at the bottom of your bathroom wastebasket. Why? You had no idea. 

You had a bit of a weird boyfriend. 

*****

After he released his bladder; Dante came back to join you in bed. 

"Hey there, stud." You smiled and let him lay his head on your tummy and hug your waist. 

"Hi, beautiful."

"How are you feeling? You okay?" 

You pushed his hair from his face and ran your fingers through it. 

"Yeah, I'm okay." Dante sighed and relaxed as you moved lower to the muscles in his back. 

"Thank you."

"For?" Your fingers stopped tickling at his skin and your brows knitted on your face. 

"For loving me and for taking my virginity." He laughed. 

At least he could say he'd been with a woman now. He couldn’t wait to tell Lady about his night; she’d be proud of him for telling you the truth and even more thrilled that he actual went though and did it with you. 

"Aw, baby. Of course I love you. You're the most amazing man I've ever met. You're so sweet and you're just the cutest thing. I love spending time with you and most importantly I love being your girlfriend. Thank you for allowing me to share such a personal and grave moment with you." You lifted his head and gave his hair a tug so he could come up to kiss you.

Dante wiggled up to your face and pressed his lips into yours. 

"Mm I love you too, and I love being your boyfriend. But I um... kind of have a question?"

"Yes?"

"... When can we do it again?" Your boyfriend grinned at you.

You just giggled lightly before pulling him into a sweet and loving kiss. 

"Mm, let's start round two then."

**Author's Note:**

> Innocent Dante is just so adorable! I really enjoyed writing him so pure and safe sex is always a win!   
> What did you guys think?  
> Feedback is always welcome <3
> 
> Also I'm still taking ideas for any DMC5 Dante works :D Just shoot me your ideas and if can make it work I shall!  
> Thank you for reading and stay tuned for more kinky demon fun ;)


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